Manganese(III) acetate-mediated oxidative cyclization of a-methylstyrene and trans-stilbene with b-ketosulfones.

Molecules

Laboratoire de Pharmaco-Chimie Radicalaire, Faculté de Pharmacie, Aix-Marseille Univ, CNRS, Institut de Chimie Radicalaire ICR, UMR 7273, 27 Bd Jean Moulin, CS 30064, 13385 Marseille Cedex 05, France.

Published: April 2013

A convenient microwave irradiation protocol was utilized for the synthesis of b-ketosulfones 1-5 in good yields. These sulfones reacted with alkenes through a radical oxidative cyclization mediated by Mn(OAc)3. Dihydrofurans 6-10 were obtained in moderate to good yields starting from 1,1-disubstituted alkenes. Dihydrofurans 11-15 were synthesized in moderate yields and unexpected cyclopropanes 16-19 were obtained in low yields starting from 1,2-disubstituted alkenes. This protocol offers access to various dihydrofurans which could be tested for their antiparasitic potential.

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Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6269865PMC
http://dx.doi.org/10.3390/molecules18044293DOI Listing

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